Exploration into Potential Functionality of Hydroxylamine-Based Compounds and Development of Novel Synthetic Processes

Teruhiko Ishikawa, Takayuki Kudoh, Seiki Saito

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Highly diverse organic reactions with hydroxylamine-based compounds have been developed during past ten decades or more and are now playing an important role in organic synthesis in a myriad of contexts. Nevertheless, we expect that there still remains useful and promising functionality for the compounds of this class. Hence, we have been making extensive efforts to disclose hidden potential of such compounds. In this report we will present some interesting and powerful organic transformations becoming available as the results of such our activities, which covers the following five novel processes or reactions: (1) silicon-tether strategy for controlling the regioselectivity and diastereoselectivity of intramolecular nitrone cycloadditions; (2) intramolecular Diels-Alder reactions employing hydroxamate tethers; (3) novel [2,3]-sigmatropic rearrangement for carbon-nitrogen bond formation; (4) dicobalt octacarbonyl-promoted rearrangement of 4-isoxazolines to acylaziridines; (5) novel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group.

Original languageEnglish
Pages (from-to)1186-1194
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume61
Issue number12
Publication statusPublished - Dec 2003

Fingerprint

Regioselectivity
Nitriles
Hydroxylamine
Cycloaddition
Silicon
Oxides
Nitrogen
Carbon
dicobalt octacarbonyl
nitrones

Keywords

  • [2,3]-sigmatropic rearrangement
  • Acylaziridines
  • Allylic amine
  • Amino polyol
  • Co(CO) promoter
  • Cycloaddition
  • Cycloisomerization
  • Intramolecular Diels-Alder reaction
  • Nitrone
  • Rearrangement of 4-isoxazolines
  • Silicon-tether

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Highly diverse organic reactions with hydroxylamine-based compounds have been developed during past ten decades or more and are now playing an important role in organic synthesis in a myriad of contexts. Nevertheless, we expect that there still remains useful and promising functionality for the compounds of this class. Hence, we have been making extensive efforts to disclose hidden potential of such compounds. In this report we will present some interesting and powerful organic transformations becoming available as the results of such our activities, which covers the following five novel processes or reactions: (1) silicon-tether strategy for controlling the regioselectivity and diastereoselectivity of intramolecular nitrone cycloadditions; (2) intramolecular Diels-Alder reactions employing hydroxamate tethers; (3) novel [2,3]-sigmatropic rearrangement for carbon-nitrogen bond formation; (4) dicobalt octacarbonyl-promoted rearrangement of 4-isoxazolines to acylaziridines; (5) novel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group.",
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